Any conflict between General Jackson and General Ashby was of a professional nature. Ashby had no professional military training, and had no particular interest in acquiring any. His habit, daily, was not to sit in a headquarters, but to personally ride the entire circuit of his picket lines. In this he frequently witnessed or partook in an extraordinary amount of skirmishing for a senior officer.
Certainly in a military way, it would have been better for Ashby to have trained other officers of his staff, etc. to conduct such observations, while he commanded from the rear, but it so happened that he was the master horseman of the Blue Ridge before the war, winning many races bareback, etc. and it was said he had traversed Northern Virginia's entire rural countryside many times over with horse, dog, and gun. For example, while he missed the action at First Manassas, he was sorry for it, as he was familiar with the ground from occasionally fox hunting upon it...
Ashby's own veterans admitted his large command was not well organized during the Valley campaign:
When Jackson attempted to place the lions' share of Ashby's cavalry under other officers, he resigned his commission, which was not accepted or forwarded by Jackson, who revoked his order. A brief account from Ashby's chaplain, J.B. Avirrett:
Ashby left issues of discipline and organization to the captains commanding the companies of his command, which swelled to something like 26 companies by the time of his death. While he had been promoted to Brigadier-General, and had a brigade worth of cavalry and artillery companies, amidst the active service he did not attend to any sort of brigade organization before his death.
Here R.P. Chew, who commanded Ashby's horse artillery battery, comments on the supposed controversy between Jackson and Ashby relative to the battle near Winchester May 25, etc. From the History of the Ashby Cavalry, or Laurel Brigade by McDonald, 1907:
Chew wrote in 1867:
Chew comments on Ashby's boldness at Jackson's defeat at Kernstown:
It is true that Jackson slapped Ashby with a feather after his death, noting he did not know of his equal as a "partisan officer":
Some of Ashby's men disliked this comment, as Ashby was an officer of volunteers, and not partisan corps, and their custom in combat was the mounted regular cavalry charge when required, and otherwise dismounted skirmishing when that was to advantage. Ashby also personally organized Chew's horse battery, the first really successful battery of horse-artillery in America since the war with Mexico, and soon to be copied to a great degree.
The brigade served under many gallant commanders during the war, but then, and after, considered themselves "Ashby's Cavalry."